Methanol → HCID 68789898, compound

HRID 1713579Notes

Reaction equation

[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]1([CH2:41][C:42]([O:44][CH3:45])=[O:43])[OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:46]O>C(OC)(OC)OC>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]1([CH2:41][C:42]([O:44][CH3:45])=[O:43])[O:40][CH3:46])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Methyl 2-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-hydroxytetrahydro-2H-pyran-2-yl)acetate (6) (1.4 g, 2.28 mmol) was dissolved in a solution of MeOH (6 mL) and trimethyl orthoformate (4 mL). PL-SO3H resin (Polymer Laboratories, 0.25 g, 3.75 mmol/g loading) was added and the reaction mixture was heated to 60° C. for 4.75 h. The mixture was filtered through cotton, rinsing with MeOH and CH2Cl2, then concentrated to a syrup (1.4 g, 99%). LC/MS tR=3.27 min, calcd for C38H42O8: 626.29, found 649.6 (M+Na)+.

Workup

additionPL-SO3H resin (Polymer Laboratories, 0.25 g, 3.75 mmol/g loading) was added
filtrationThe mixture was filtered through cotton
washrinsing with MeOH and CH2Cl2
concentrationconcentrated to a syrup (1.4 g, 99%)

Sources & evidence

ORD record: ord-5964dd11770c400dbe1c151b33a0a9fe
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795228B2

Reaction notes

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